Dicyclohexylcarbodiimide → N-Methanesulfonyl-5-[8-(morpholin-4-yl)-2-[(quinolin-2-yloxy)methyl]imidazo[1,2-a]pyrazin-5-yl]pyridine-2-carboxamide

Participants

Reaction Steps

To a solution of compound 15c (400 mg, 0.790 mmol) in DCM (20 mL) was added methanesulfonamide (78.8 mg, 0.830 mmol), DCC (256 mg, 1.24 mmol) and 4-dimethylaminopyridine (152 mg, 1.24 mmol). The reaction mixture was stirred at rt overnight, and was quenched with H2O (40 mL). The resulting mixture was extracted with DCM (3×40 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel, eluting with DCM/MeOH (10:1 v/v). The title compound 76 was obtained as a yellow solid (307 mg, 69% yield). 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 8.99 (s, 1H), 8.27-8.19 (m, 3H), 8.08 (s, 1H), 7.89 (d, J=7.8 Hz, 1H), 7.79 (d, J=8.4 Hz, 1H), 7.68 (t, J=6.9 Hz, 1H), 7.56 (s, 1H), 7.47 (t, J=6.9 Hz, 1H), 7.05 (d, J=8.7 Hz, 1H), 5.58 (s, 2H), 4.41-4.20 (m, 4H), 3.88-3.71 (m, 4H), 3.05 (s, 3H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C27H25N7O5S: 560.2 (M+H). Found 560.0.

Provenance & Evidence